Thursday, alleging that the county, Sheriff Craig Roberts and two of his top aides knew the man was dangerously unstable but failed to intervene.

Roberts and other defendants knew Sgt. Jeffrey A. Grahn presented a threat to his wife, Charlotte, and that he was emotionally unsteady, angry, depressed and had substance-abuse problems, according to the wrongful-death lawsuit filed in Multnomah County.

On Feb. 12, 2010, Grahn confronted Charlotte Grahn and two of her friends, Victoria Schulmerich and Kathleen Hoffmeister, at the M&M Restaurant & Lounge.

Grahn, who was legally drunk, entered the Gresham bar, argued with his wife and threw a drink in Schulmerich's face. He then grabbed Charlotte Grahn by her hair, pulled her outside and shot her in the head with a Glock .40-caliber pistol. He returned to the bar with his gun drawn and killed Schulmerich and Hoffmeister with shots to the head.

Grahn again went outside and, standing next to his wife's body, committed suicide.

View full sizeBrent Wojahn/The OregonianAshley Grahn holds her brother, Kyle Grahn, during a 2010 remembrance in Gresham's Main City Park for their mother, Charlotte.

The Schulmerich and Hoffmeister families each are seeking $3.5 million for loss of companionship and the women's pain and suffering. The families are asking almost $1 million more in lost earnings and expenses.

The family of Charlotte Grahn has not filed a lawsuit and has until 5 p.m. Friday to do so.

A year before the killings, the Sheriff's Office received reports that Grahn was abusive and potentially explosive and asked the Portland Police Bureau to investigate.

"The Sheriff's Office knew that Grahn was violent, abusive, and out of control. They were specifically warned that he was likely to kill his wife, his family, and himself. Nonetheless, the Sheriff's Office intervened to prevent the Portland Police from sending their investigation of Grahn to the Clackamas County District Attorney. Now, four people are dead," said

If the case goes to trial, it will shed light on how the Sheriff's Office and other law enforcement agencies handle domestic violence issues involving their employees. Roberts and Clackamas County District Attorney John Foote or his second-in-command could be called to testify.

The DA's office maintains it should be advised of domestic violence incidents involving sheriff's deputies.

The county received a copy of the lawsuit Thursday afternoon but declined to address the allegations. “At the insistence of the county counsel, the Clackamas County Sheriff’s Office will offer no specific comments in the matter of former employee Jeffrey A. Grahn,” Sgt. James Rhodes, sheriff’s spokesman, said in a statement. “Our heartfelt condolences go out to the victims of this tragedy, their families and all those affected.”

According to police reports obtained by The Oregonian, Charlotte Grahn allegedly told one of her husband's co-workers, a deputy, that she was the victim of domestic violence but the deputy did not report the incident.

The reports also show that a couple -- both law enforcement officers and long-time friends of the Grahns -- told the Sheriff's Office they had serious concerns about Jeffrey Grahn's behavior. The friends and Charlotte Grahn's sister "fear .. that they will receive a phone call one day that Jeffrey has killed everybody in his family then himself," according to a report written by Undersheriff Dave Kirby in April 2009, 10 months before the shootings. One of the friends said Grahn had "gone off the deep end" and drinks "like there's no tomorrow," Kirby noted.

Charlotte Grahn told an investigator that Jeffrey Grahn exhibited signs of depression and suicidal behavior and was worried that if it became known he had obtained a prescription for anti-depressants, it could affect his employment.

Portland police routinely enlist help from the district attorney's office when investigating domestic violence involving officers and requested that the Clackamas County District Attorney be brought in.

Clackamas County sheriff's Lt. Graham Phalen, who is assigned to the internal affairs unit, asked investigators to "hold off" on contacting the district attorney's office, according to a memo written by one of the Portland investigators. Phalen also was named as a defendant in the lawsuit filed by the Schulmerich and Hoffmeister families.

Phalen concluded that the evidence did not support criminal charges against Grahn.